2-Acetyl-2-(3-butenyl)-γ-butyrolactone | 132103-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-Acetyl-2-(3-butenyl)-γ-butyrolactone
• 英文别名: 3-Acetyl-3-but-3-enyloxolan-2-one
• CAS: 132103-05-0
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: IMSZAVAJZWORMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Acetyl-2-(3-butenyl)-γ-butyrolactone 在 samarium diiodide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以87%的产率得到(5R^*,6S^*,7S^*)-6-Hydroxy-6,7-dimethyl-2-oxaspiro<4.4>nonan-1-one
  参考文献：
  名称：

  二碘化sa促进的立体控制的分子内酮-烯烃还原偶联反应

  摘要：

  报道了不饱和β-酮酸酯和β-酮酰胺的立体控制的分子内偶联。在此过程中产生了高收率的高度取代的β-羟基环戊烷羧酸酯，并在三个连续的立体中心进行了大量且可预测的立体化学控制。

  DOI：

  10.1016/s0040-4039(00)96511-0

文献信息

• Intramolecular reductive coupling reactions promoted by samarium diiodide
  作者：Gary A. Molander、Caryn Kenny

  DOI：10.1021/ja00203a027

  日期：1989.10

  Samarium diiodide is a useful reagent for promoting intramolecular reductive coupling reactions, generating functionalized carbocycles. Ketone-olefin coupling, pinacolic coupling, and other related reductive coupling reactions are accomplished under mild conditions with samarium diiodide. Products are accessed in high yield, and in many cases excellent stereochemical control is achieved at three contiguous

  二碘化钐是促进分子内还原偶联反应、生成功能化碳环的有用试剂。酮-烯烃偶联、频哪醇偶联和其他相关的还原偶联反应是在温和条件下使用二碘化钐完成的。产品以高产率获得，并且在许多情况下在三个相邻的立体中心实现了出色的立体化学控制。讨论了控制这些反应立体化学结果的因素，并概述了机械方面的考虑。
• Sequential radical cyclization/intermolecular carbonyl addition reactions initiated by samarium(II) iodide
  作者：Gary A. Molander、Caryn Kenny

  DOI：10.1021/jo00004a020

  日期：1991.2

  A sequential reductive coupling process promoted by samarium (II) iodide (SmI2) is described. Thus, ethyl 2-acetyl-2-methyl-5-hexenoate, upon treatment with SmI2 in the presence of a variety of aldehydes or ketones, undergoes an initial radical (ketyl) olefin cyclization. Subsequent reduction of the intermediate radical generated in this process produces a transient organosamarium species which can be trapped in situ by the added aldehyde or ketone electrophiles. Through this sequential radical cyclization/intermolecular carbonyl addition reaction, two new carbon-carbon bonds are generated in a one-pot process. Furthermore, a high degree of stereochemical control is established over three contiguous stereocenters, markedly increasing molecular complexity from the starting materials to the observed products.
• MOLANDER, GARY A.;KENNY, CARYN, J. AMER. CHEM. SOC., 111,(1989) N1, C. 8236-8246
  作者：MOLANDER, GARY A.、KENNY, CARYN

  DOI：——

  日期：——
• MOLANDER, GARY A.;KENNY, CARYN., J. ORG. CHEM., 56,(1991) N, C. 1439-1445
  作者：MOLANDER, GARY A.、KENNY, CARYN.

  DOI：——

  日期：——
• Stereocontrolled intramolecular ketone-olefin reductive coupling reactions promoted by samarium diiodide
  作者：Gary A. Molander、Caryn Kenny

  DOI：10.1016/s0040-4039(00)96511-0

  日期：1987.1

  The stereocontrolled intramolecular coupling of unsaturated β-ketoesters and β-ketoamides is reported. Good yields of highly substituted β-hydroxycyclopentanecarboxylates are generated in the process, with substantial and predictable stereochemical control at three contiguous stereocenters.

  报道了不饱和β-酮酸酯和β-酮酰胺的立体控制的分子内偶联。在此过程中产生了高收率的高度取代的β-羟基环戊烷羧酸酯，并在三个连续的立体中心进行了大量且可预测的立体化学控制。